(S)-(3-(hydroxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)(3-methoxyphenyl)methanone | 939027-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (S)-(3-(hydroxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)(3-methoxyphenyl)methanone
• CAS: 939027-72-2
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: BOJXIOWYBYROAD-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-(3-(hydroxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)(3-methoxyphenyl)methanone 在 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-butyl-11-[[(3S)-2-(3-hydroxybenzoyl)-3,4-dihydro-1H-isoquinolin-3-yl]methoxy]undecanamide
  参考文献：
  名称：

  Identification of a series of tetrahydroisoquinoline derivatives as potential therapeutic agents for breast cancer

  摘要：

  A series of tetrahydroisoquinoline-N-phenylamide derivatives were designed, synthesized, and tested for their relative binding affinities, and antagonistic activities against estrogen receptor (ER). Compound If (relative binding affinity, RBA = 5) showed higher binding affinity than tamoxifen (R BA = 1), a potent ER antagonist and currently being used for breast cancer therapy. Compound If also exerted optimal antagonistic activity against ER in reporter and cell proliferation assays. Interestingly, compound Ij, which only has a minor agonistic effect against ER, acted as a progesterone receptor (PR) antagonist and exerted agonistic activity against AP-1 through ER pathway. Our results show that these new compounds can be employed as leading pharmacophore for further development of potent selective ER and/or PR modulators or antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.002
• 作为产物：
  描述：

  (S)-(-)-1,2,3,4-四氢-3-异喹啉甲醇 、 3-甲氧基苯甲酸 在 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-(3-(hydroxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)(3-methoxyphenyl)methanone
  参考文献：
  名称：

  Identification of a series of tetrahydroisoquinoline derivatives as potential therapeutic agents for breast cancer

  摘要：

  A series of tetrahydroisoquinoline-N-phenylamide derivatives were designed, synthesized, and tested for their relative binding affinities, and antagonistic activities against estrogen receptor (ER). Compound If (relative binding affinity, RBA = 5) showed higher binding affinity than tamoxifen (R BA = 1), a potent ER antagonist and currently being used for breast cancer therapy. Compound If also exerted optimal antagonistic activity against ER in reporter and cell proliferation assays. Interestingly, compound Ij, which only has a minor agonistic effect against ER, acted as a progesterone receptor (PR) antagonist and exerted agonistic activity against AP-1 through ER pathway. Our results show that these new compounds can be employed as leading pharmacophore for further development of potent selective ER and/or PR modulators or antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.002